Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, HPLC of Formula: C7H5NOS, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5NOS

Preparation 125; 2- (thieno [3, 2-b] pyridin-7-yl) acetamide; 7-Bromo-thienoF3, 2-blpyridine; Heat phosphorus oxybromide (145.00 g, 0.50 moles) to 60 C to form a melt. Add thieno [3, 2-b]-7-pyridinol (14.73 g, 97.43 mmol) while stirring and increase heat to 100 C for 2 hours. Pour the reaction contents over ice (1.0 kg). Dilute the slurry with ice and water to about 3 L. Extract the aqueous solution with chloroform (4 X 500 mL). Make the aqueous solution basic (pH 10-11) with 2 N sodium hydroxide and reextract with chloroform (3 X 400 mL). Treat the organic layers with magnesium sulfate, filter and concentrate. Redissolve the crude solid in dichloromethane (100 mL) and load the solution onto silica (300 g). Elute with 2 L of 30% ethyl acetate/dichloromethane. Concentrate the eluent to yield the desired compound as a crystalline solid (18.68 g, 89.5%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69627-02-7, Thieno[3,2-b]pyridin-7(4H)-one, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2003/76442; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 944937-53-5, name is 6-Bromo-1H-pyrrolo[3,2-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Bromo-1H-pyrrolo[3,2-b]pyridine

To a mixture of 6-bromo-lH-pyrrolo[3,2-b]pyridine (0.985 g, 5 mmol, 1 eq) in N,N- dimethylformamide (25ml) was added cesium carbonate (1.79 g, 5.5 mmol, 1.1 eq), followed by (1,4,4- trifluorocyclohexyl)methyl trifluoromethanesulfonate (1.50 g, 5 mmol, 1 eq). The mixture was stirred at 70 C for five hours. The mixture was quenched with water, and extracted with ethyl acetate which was washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated down. The sample was purified by flash chromatography eluting with 40% ethyl acetate in hexane, then triturated with hexanes to provide 1.63 g (93.9%) of product as a solid (24, 1.63 g, 93.9%), MS (ESI) [M+H+]+ = 347.0, 349.0.

With the rapid development of chemical substances, we look forward to future research findings about 944937-53-5.

Reference:
Patent; ZHANG, Jiazhong; BUELL, John; CHAN, Katrina; IBRAHIM, Prabha, N.; LIN, Jack; PHAM, Phuongly; SHI, Songyuan; SPEVAK, Wayne; WU, Guoxian; WU, Jeffrey; WO2014/145051; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 71902-33-5, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 71902-33-5, name is 3,5-Difluoropyridine. A new synthetic method of this compound is introduced below.

INTERMEDIATE 63 : 3, 5-Difluoro-4-tributylstannanyl-pyridine [00224]. n-Butyl lithium (1.0 eq, 76 mmol, 47.6 mL, 1.6 M in hexanes) was added via dropping funnel to a solution of diisopropylamine (1.05 eq, 80 mmol, 11.2 mL) in THF (300 mL) at-78 °C under nitrogen (N2). The solution was stirred for 30 min at-78 °C, then a solution of 3,5- difluoropyridine (1.05 eq, 80 mmol, 9.2 g) in THF (20 mL) was added dropwise via syringe. A beige precipitate was observed to form. The reaction stirred at-78 °C for 90 min then tributyltin chloride (1.0 eq, 76 mmol, 20.7 mL) was added dropwise via syringe and the resulting solution allowed to warm to RT over 2 h. Water (5 mL) was added, then roughly 250 mL of THF was removed on a rotary evaporator. The resulting material was diluted with diethyl –139– ether (350 mL) and washed successively with water (2X200 mL), saturated sodium chloride solution (1X150 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford the 3,5-Difluoro-4-tributylstannanyl-pyridine as a colourless oil (27.5 g, 88percent). This material was used crude without further purification. Retention Time (LC, method: ammonium acetate standard): 3.35 min. MS (M+H+) : 406.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71902-33-5, its application will become more common.

Reference:
Patent; MILLENIUM PHARMACEUTICALS, INC.; WO2004/92167; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 103041-38-9, name is Ethyl 3-(pyridin-2-ylamino)propanoate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C10H14N2O2

EXAMPLE 1 Preparation of Ethyl 3-[[4-(methylamino)-3-nitrobenzoyl](pyridin-2-yl)amino]-propanoate (II) 100 g of compound I was dissolved in 1 L of dichloromethane under nitrogen atmosphere and cooled to 0-5 C. Thionyl chloride was added to the reaction mixture for 1 h and the reaction mixture was boiled to reflux. Maintained the reaction mass under the same temperature for 5-6 h. After completion of the reaction, excess thionyl chloride was removed by co-distillation with dichloromethane and finally the solvent was completely removed under vacuum. The acid chloride was then dissolved in dichloromethane under an inert atmosphere and triethyl amine was added to the reaction mixture. To the reaction mixture was added slowly a solution of ethyl-3-(pyridine-2-ylamino) propanoate in dichloromethane. The reaction mixture was maintained at the same temperature for another 6-12 h. After completion of the reaction, the reaction mass was diluted water and extracted the product with dichloromethane. The combined organic layers were separated and dried over anhydrous sodium sulphate. The solvent was distilled off under vacuum and the product was purified by hexane. Yield: 80%, HPLC: >98%

With the rapid development of chemical substances, we look forward to future research findings about 103041-38-9.

Reference:
Patent; Biophore India Pharmeuticals PVT. Ltd.; Pullagurla, Manik Reddy; Rangisetty, Jagadeesh Babu; Nandakumar, Mecheril Valsan; (8 pag.)US2015/246900; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6283-81-4 ,Some common heterocyclic compound, 6283-81-4, molecular formula is C10H11NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

2-Ethyl-5-pyridin-3-yl-2H-pyrazol-3-ol: To 3-oxo-3-pyridin-3-yl-propionic acid ethyl ester (500 mg, 3.57 mmol) in AcOH was added ethylhydrazine oxalate (231.9 mg, 3.86 mmol) and the mixture refluxed for 16 h. After which, the AcOH was evaporated and crude mass neutralized with aq. Na2CO3 solution. Following extraction with EtOAc, the organic phase was washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography using 2% MeOH-DCM as an eluent to give 2-ethyl-5-pyridin-3-yl-2H-pyrazol-3-ol (110 mg, 22.5%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6283-81-4, its application will become more common.

Reference:
Patent; Hoffmann-La Roche Inc.; Bhagirath, Niala; Brameld, Kenneth Albert; Kennedy-Smith, Joshua; US2013/90333; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 677728-92-6 ,Some common heterocyclic compound, 677728-92-6, molecular formula is C6H4FNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

[001077] A mixture of 6-fluoronicotinaldehyde (4.7 g, 37.6 mmol) and titanium isopropoxide (1.37 g, 75.2 mmol) in dry THF (90 mL) was stirred at r.t. for 30 mins under nitrogen. Then a solution of 2-methyl-2-propanesulfinamide (4.56 g, 37.6 mmol) in dry THF (10 mL) was added. The reaction mixture was stirred at r.t. for 16 h, diluted with EtOAc (200 mL) and MeOH (50 mL), and then brine (100 mL) was added slowly. The mixture was stirred at r.t. for 30 mins and filtered. The solid was washed with EtOAc (200 mL x 2). The filtrate was extracted with EtOAc (200 mL x 3). The combined organics were washed with brine (50 mL x 2), dried over Na2S04, and concentrated. The residue was purified by SGC (PE/EtOAc = 5/1) to give the title compound. LC-MS: m/z = 303 (M+H)+, RT = 1.61 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; QUARTET MEDICINE, INC.; ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL); TEBBE, Mark, Joseph; ATTON, Holly, Victoria; AVERY, Craig; BROMIDGE, Steven, Mark; KERRY, Mark; KOTEY, Adrian, Kotei; MONCK, Nathaniel, J.; MENICONI, Mirco; RIDGILL, Mark, Peter; TYE, Heather; SAIAH, Eddine; JOHNSSON, Kai, Peter; GORSKA, Katarzyna, Irena; PENG, Hairuo; MCCALL, John, Michael; (356 pag.)WO2017/59191; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15197-75-8, 3-(2-Pyridyl)propionic Acid, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C8H9NO2, blongs to pyridine-derivatives compound. Computed Properties of C8H9NO2

General procedure: In air, a round bottom flask was charged with [Pd(mu-Cl)(Cl)(NHC)]2 (0.2 mmol, 225 mg), 2-pyridylacetic acid hydrochloride(0.4 mmol, 70 mg), KOtBu (1.0 mmol, 112 mg) and THF(2.0 mL). After stirring for 6 h at room temperature, the mixturewas condensed under vacuum. The solid residue was filtered byflash chromatography on short silica gel with CH2Cl2 and recrystallizedfrom n-hexane/CH2Cl2 to provide the desired products.

The synthetic route of 15197-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Wei; Yang, Jin; Journal of Organometallic Chemistry; vol. 872; (2018); p. 24 – 30;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 73781-91-6, Adding some certain compound to certain chemical reactions, such as: 73781-91-6, name is Methyl 6-chloronicotinate,molecular formula is C7H6ClNO2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 73781-91-6.

f) 6-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]-triazol-4-ylmethoxy)-nicotinic acid methyl ester A solution of (3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-methanol (158 mg, 0.83 mmol) in THF (2.4 mL) was added dropwise at 0 C. to a suspension of NaH (60% in oil, 40 mg, 0.91 mmol) in THF (1.2 mL) and the reaction mixture was then stirred at room temperature for 30 min. Then a solution of methyl 6-chloronicotinate (157 mg, 0.91 mmol) in THF (2.4 mL) was added dropwise at 0 C. and the reaction mixture stirred at room temperature for 18 h. The mixture was then poured into water extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (209 mg, 77%) as a white solid. MS: m/e=326.1 [M+H]+.

According to the analysis of related databases, 73781-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hernandez, Maria-Clemencia; Lucas, Matthew C.; Thomas, Andrew; US2012/115844; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109-09-1 ,Some common heterocyclic compound, 109-09-1, molecular formula is C5H4ClN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: A mixture of 2-chloro-5-methyl-benzimidazole (10.2 g, 61.2 mmol) and hydrazine monohydrate (59 mL, 1.22 mol) was stirred at 100 C overnight. After being cooled to ambient temperature, to the reaction mixture was added to water (60 mL). After stirring under ice cooling, the resulting precipitates were collected by filtration. The precipitates were washed with water 3 times, and then dried in vacuo to give 2-hydrazino-5-methyl-benzimidazole (8.4 g, 84.6%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109-09-1, its application will become more common.

Reference:
Article; Nakao, Syuhei; Mabuchi, Miyuki; Shimizu, Tadashi; Itoh, Yoshihiro; Takeuchi, Yuko; Ueda, Masahiro; Mizuno, Hiroaki; Shigi, Naoko; Ohshio, Ikumi; Jinguji, Kentaro; Ueda, Yuko; Yamamoto, Masatatsu; Furukawa, Tatsuhiko; Aoki, Shunji; Tsujikawa, Kazutake; Tanaka, Akito; Bioorganic and Medicinal Chemistry Letters; vol. 24; 4; (2014); p. 1071 – 1074;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 128071-98-7 ,Some common heterocyclic compound, 128071-98-7, molecular formula is C5H3BrFN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Synthesis of Compound 35.1 [0308] To a solution of 4-bromo-2-fluoropyridine (5.0 g, 28.6 mmol, 1.0 eq) in THF (50 mL) were added 2, 2′-oxydiethanol (9.1 g, 85.8 mmol, 3.0 eq) and t-BuOK (3.8 g, 34.3 mmol, 1.2 eq). After stirred at room temperature for 12 h, the reaction mixture was diluted with water (20 mL) and extracted with EA (20 mL x 3). The combined organic layers were washed with brine (20 mL x 5), dried over anhydrous Na2S04 , and concentrated under reduced pressure. The residue was purified by chromatography column (PE : EA = 3 : 1) to give 35.1 (6.4 g, yield: 86%) as a yellow oil; ESI-MS (M+H)+: 262.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,128071-98-7, its application will become more common.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem